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Why Jon Lester may (or may not) be traded this week

"I don't see that happening. I don't see him getting traded," the Red Sox designated hitter said regarding Jon Lester. "The signing thing, I don't know what the situation is with that, but hopefully they understand that he is very important."

Well, there is a chance Lester is still a member of the Red Sox come Thursday night. Then again ...

The Red Sox and Lester find themselves in a position with a few days to go before the non-waiver trade deadline few thought was coming, even as recently as a month ago. There is a very real possibility -- a very real possibility -- that the Sox ace could be dealt.

It's impossible to ignore the signs.

As of Monday night, there were no signs that the Red Sox would be making one last bid at engaging Lester in contract extension talks. While there has still only been one firm offer, both sides have offered enough evidence that there is an understanding of the current comfort level for each party.

It is believed the Red Sox have yet to approach what has been established as market value. (Think in the neighborhood of five years, $120 million.) Without the insinuation from the organization that such a level would be acceptable, there hasn't been a willingness to re-engage. That doesn't figure to change before Thursday's deadline.

The approach by the Red Sox is consistent with their past negotiations: start low and attempt to get as much cost certainty as possible before reaching their ultimate comfort level.

This will not be Cole Hamels punctuating his contract extension negotiations just prior to the conclusion of July 2012. For whatever reason, the Red Sox simply aren't ready to take the leap of faith the Phillies did two years ago.

"Not at all," said Ortiz when asked if he was surprised at the evolution of Lester's negotiations. "When you're buying you want to get things as cheap as you can. There's nothing wrong with that. Now there is value out there. I can tell you right now how much Lester costs just because the numbers you can see. It's not a secret anymore. So if you're not going to get close to that, it's not going to happen. This is the time for him to talk about a contract because he's playing, in a good situation and he has to pull out the best out of them. Is he going to get a contract after this one? I don't know. But you have to get what you deserve in this one."

Right now, the Red Sox' idea of a ceiling isn't matching up with Lester's, particularly when it comes to the number of years. Judging by principal owner John Henry's previous comments stating a hesitancy to go beyond four years for a pitcher in his 30s, it's highly possible the two sides will never see eye to eye in that respect.

Certainly, right now there is no common ground. And without that, and the price seemingly only going up with two months to go before season's end, it is leading to the logical conclusion that the Red Sox' best move is to get something significant for Lester.

If no deal is reached, there might be little reason to hang on to the lefty for the season's final two months.

The Red Sox could make the case that they can use the schedule's home stretch to ensure Lester's health before making their best bid. But the problem with that is that with each passing day the pitcher's worth rises (barring any physical setbacks), and once he gets to the exclusive negotiating period there are no intentions of not exploring free agency.

It really has gotten to the point that Lester can sniff the finish line.

Whether he's with the Red Sox or the team that trades for him, the starter is ready to explore the world of the open market. That doesn't mean any new club won't put its best foot forward, as the lefty's teammate points out.

"Trust me, if he gets traded, he goes somewhere else, they are going to be waiting for him in the clubhouse with a contract, with a deal," Ortiz said. "'Here, we've got this for you, that's why we traded for you.' That's how it works. Whomever trades for him is going to have a guaranteed contract on the table for him. They're not going to give prospects or whatever they give away just to use him just for a couple of months. I don't see that happening."

The reality is, however, that Lester almost certainly will be a rental for whatever team might acquire him. That means he won't fetch as much as David Price, or even teammate John Lackey (he of the major league minimum contract in 2015). But that doesn't mean it wouldn't be worth it for the Red Sox to use their top starter as a means to an end.

This is perhaps the Red Sox' best chance to find that elusive impact bat, whether it's in the form of a straight-up trade or via acquiring pieces that they can use to reel in a major league-ready slugger. Jake Peavy hauled in more than most thought, and last year's top rental -- Matt Garza -- netted the Cubs their top pitching prospect (C.J. Edwards), along with a potential power bat (Mike Olt) and a pretty good reliever (Neil Ramirez).

The Red Sox' perfect scenario might be to get their big payoff courtesy a deal this week, and then loop back with Lester at season's end and fire off a next-level offer. They almost certainly couldn't match the best offer in free agency, but with the lefty's willingness to take as much as a year less (but most likely not anything less than five years) the Sox could accept the invitation to get back into a conversation they haven't yet entered ... with a high-ceiling, trade-induced player, to boot.

There also is the blueprint Lester doesn't get moved. That script is based on the hope he stays healthy and gets to the end of the season in the mood to lock up something with the Red Sox. But, once again, the problem is that if he gets that far down the road there likely will be no stopping him from hitting the market. And as for an acceptable trade, it's hard to believe, with Lester's pedigree, that the Sox couldn't do better than the Cubs' haul of a year ago.

The somewhat unexpected fly in the ointment might be Lackey's reported availability. While it's easy to see why the veteran righty would be desirable for a contender (considering his contractual commitment for '15) it's hard to imagine the Red Sox would be willing to part with both Lester and Lackey. That would leave a fairly daunting rebuild for the team's starting rotation a season from now.

It's a decision Lester and the Red Sox weren't hoping to be slapped with. But, like it or not, it's here.

"It's not like what you really want," Ortiz explained, "but at some point if negotiations are going bad you have to get your mind right and get prepared for whatever."

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